The synthesis of 18beta-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects in leukemia cells.

Abstract

18beta-Glycyrrhetinic acid (GA), 3beta-hydroxyl-11-oxo-olean-12-ene-29-oic acid, has been found to inhibit growth and to induce apoptosis in cancer cells. Through structural modification, 16 GA derivatives (12 novel compounds) with modified structures at the C(3) and C(29) positions were synthesized. The antiproliferative effects and apoptosis induction abilities of these compounds were determined in human leukemia HL-60 cells. The replacement of the hydroxyl group of GA with a carbonyl group or an oxime group at C(3) position does not influence the antiproliferative effect. However, the antiproliferative and apoptosis induction abilities of the compounds with a replaced alkoxyimino group at position C(3) and a free C(29) carboxyl group are markedly increased.

• Authors: Dan Liu, Dandan Song, Gang Guo, Rui Wang, Jinling Lv, Yongkui Jing, Linxiang Zhao
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 15 Issue 16 Pg. 5432-9 (Aug 15 2007) ISSN: 0968-0896 [Print] England
• PMID: 17566745 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Glycyrrhetinic Acid

Topics

• Apoptosis (drug effects)
• Cell Proliferation (drug effects)
• Glycyrrhetinic Acid (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
• HL-60 Cells
• Humans
• Leukemia (pathology)
• Molecular Structure